


Last Good Night, First Good Day

by DarcyDelaney



Category: Supernatural
Genre: Alternate Universe - Reality Show, Dancing, Dean swears a lot, Flirty Dancing, Fluff, M/M, Meet-Cute
Language: English
Status: Completed
Published: 2020-05-19
Updated: 2020-05-19
Packaged: 2021-03-02 21:00:11
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,617
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24273199
Author URL: https://archiveofourown.org/users/DarcyDelaney/pseuds/DarcyDelaney
Summary: There are three things to know about Dean Winchester.One: He’s not easily coerced into things when he’s drunk. Two: He doesn’t do shorts. Three: He doesn’t dance.He still doesn’t do shorts, but the other two, apparently, are now fair game.
Relationships: Castiel/Dean Winchester
Comments: 9
Kudos: 74





	Last Good Night, First Good Day

**Author's Note:**

> I guess my shtick is to take Dean and Cas and throw 'em into different reality shows...can't say I'm upset about it.
> 
> Massive thanks to the lovely [Banshee1013](https://archiveofourown.org/users/Banshee1013/pseuds/Banshee1013) for lending beta talents, and the wonderful [NikkiSage](https://archiveofourown.org/users/NikkiSage/pseuds/NikkiSage) for brainstorming titles, summaries, and general pieces of this fic with me. You both are fabulous <3!
> 
> Lastly...have you guys seen Flirty Dancing? You should watch Flirty Dancing. (btw, the song Dean and Cas dance to is ["What A Man Gotta Do"](https://www.youtube.com/watch?v=XejVB_fba04) by the Jonas Brothers.)

There are three things to know about Dean Winchester.

One: He’s not easily coerced into things when he’s drunk. Two: He doesn’t do shorts. Three: He doesn’t dance.

He still doesn’t do shorts, but the other two, apparently, are now fair game.

Dean stands at Buckingham Fountain in the middle of Grant Park, hands gripping the railing in front of him that’s running around it, as Garth, a member of the makeup crew who’s just as odd as he is endearing, nudges a few stray hairs into place before slamming him with another shot of hairspray.

“No warning this time, huh?” he says, channeling his inner diva for a second with an overdramatic cough.

“Sorry,” Garth says, spinning the bottle of hairspray between his fingers like a sharpshooter before tucking it back into his supply belt and grabbing a small sponge. “Time is of the essence right now. Word is your partner’ll be here any minute. Just a few more things to fix up here...”

Dean waits until Garth’s not looking to roll his eyes, trying not to blink or sneeze as the guy starts tapping the sponge against his cheekbone. He’s always liked to think of himself as a good-looking dude, but he may as well be goddamn Jabba the Hut with the amount of time Garth’s spent on him for what’ll amount to a three-minute spot.

He closes his eyes and holds his breath to avoid fucking up Garth’s work while also trying—and failing—to stay ahead of the panic attack he can already feel coming. The sponge disappears a few seconds later and he opens his eyes hesitantly.

“We good?”

“Good? You look great, my man!” Garth says, clapping Dean on the back hard enough for him to stumble forward a bit, pressing himself further up against the railing. “Knock ‘em dead!”

Dean chuckles hollowly, glancing down at the shiny wingtips that look like fucking clown shoes on him. No matter how much he’d tried to protest, wardrobe had insisted on the fucking things, on the whole fucking outfit, a soft gray sweater and dark jeans that actually fit him. It’s all gotta cost more than what he makes in a month and he’s got plenty of perfectly fine clothes hanging in his closet—fine, tossed on the floor—but _noooo_ , break the bank on something he’ll never fucking wear again.

When he looks back up, Garth’s gone, and Dean can feel himself getting tense again. This shit just became a lot more real without him. He tightens his grip on the railing, listening for any kind of acknowledgement from the show’s host, a smarmy British chick named Bela Talbot who Dean finds equal parts hot and terrifying. They probably could’ve found a more personable host, but she’s some kind of ballroom superstar, so nabbing her was probably a Herculean effort in and of itself.

“Dean, sweetie,” she calls from behind him, “your partner’s just arrived, so do try and look a little more like you may be about to meet the love of your life, and just a smidge less like you’re on Death Row, hmm?”

Dean clenches his teeth in what he hopes even slightly resembles a smile, even though he’s not facing the camera and no one can see him. “Yep.”

He hates this, hates having his back to everyone and everything. He’s vulnerable, just standing here like a goddamn lovesick moron. He bites his lower lip, watching the way his knuckles are turning whiter and whiter around the railing and cursing his past self for, well...everything.

* * *

“All right, all right, all right,” Dean says, leaning hard into the comfortable buzz he’s feeling as he drops back down onto the couch with a fresh beer in hand. He grabs for the remote and is about to hit PLAY when Benny stops him, covering the remote with his hand while keeping his eyes glued to his phone.

“Slow your roll, McConaughey.”

Dean stares at him, feeling way more betrayed than he has the right to, but so what if he’s being dramatic—it’s been a long week, he’s well on his way to drunk, and he just wants a night of shitty horror movies with his best friends.

“You fellas ever heard of something called _Flirty Dancing_?” Benny asks, completely ignoring Dean’s melodramatics next to him.

He holds the phone closer to his face as he squints against the light. Dean rolls his eyes and snatches the phone to try and read it for himself, but apparently the booze has other ideas, and he scoffs when the alcohol makes it seem like the words won’t stop moving on the screen.

“C’mon, man, ‘s where people dance...all flirty,” he says. “O’viously.”

Sam looks at him flatly, and Dean raises his hands in surrender. “What? ‘S what it is, Sammy. Can we get back to the homicidal robot security guards, please?” he asks, gesturing toward the TV with his bottle.

“Gimme that,” Sam says instead, and before Dean can do anything about it, Sam’s fucking bear hands swoop in out of nowhere and grab the phone. Dean blinks, then waves him away dismissively.

“G’head,” he mutters, taking a long sip of his beer. “Take it. I don’t care.”

Sam doesn’t even acknowledge him, eyes scanning the screen like he’s reading some kind of stupid law document. For lawyering. “It’s a dating show,” he says slowly, brows furrowing together as he continues, “...with dancing.”

Dean cackles, smacking Sam’s shoulder—a little harder than he’d meant to, so sue him. “See? What’d I tell ya?”

Sam rolls his eyes. “You’re drunk, dude.”

“Y...y’re...fuck you.”

Benny laughs. “Y’re shittin’ me.” He shakes his head, still grinning as he cracks open another beer. “They’ll try to sell us on anything these days.”

“‘Looking for love in all the wrong places?’” Sam reads, tapping the screen to keep it lit. “‘Have you tried the dance floor?’”

“Jesus Christ,” Dean mutters, sinking back deeper into the couch and tipping his latest bottle back.

“‘CWTV’s newest hit show, _Flirty Dancing_ , is coming to Lawrence, and we’re looking for Dancing Kings and Queens as contestants! No experience necessary! Join ballroom superstar Bela Talbot as she coaches hopeful singles in choreographed dance numbers designed to get the blood flowing to all the right places…’” Sam trails off and makes a face. “Gross. Uh…‘Think you’ve got what it takes? We want to hear from you! Fill out our questionnaire and submit it along with a headshot to contestants@cwtv.com.’”

Dean looks at Benny suspiciously. “Where’d you even find this, man?”

Benny opens his mouth to answer, but before he can, Charlie interrupts as she returns to the living room from the kitchen. “What’re we talking about?” She heads over to the couch, nursing a fancy-looking green drink garnished with a cherry that looked way more tempting to Dean than it has any right to be. “Shove over, Winchester,” she says, dropping down between Dean and Benny without waiting for them to make room.

“New reality show,” Sam says. “With dancing.”

Charlie raises her eyebrows, purses her lips in contemplation, then nods. “I’d watch it.”

Jesus, what does he have to do to get these people to just watch the fucking movie? Maybe if he’s more direct... “Yeah, sure, okay, but for tonight, can we just watch the fucking movie, please?”

“You should do it, Dean,” Sam says, handing the phone back over to Benny before elbowing his older brother with a grin and a waggle of his eyebrows. “No experience necessary.”

Dean coughs in surprise, trying and failing to stop some of his mouthful of beer from dribbling out onto his shirt. “Yeah, okay.”

“You _would_ look pretty dapper in a tux,” Charlie muses.

“Okay, we are _not_ having this conversation,” Dean snaps, reaching across Charlie’s lap for the remote. “I signed up for _Chopping Mall_ , not some random-ass dating show—”

“It’s a dating show?!” Charlie grabs the phone from Benny and starts typing. “We’re doing this right now.”

Dean’s eyes go wide. “Uh, fuck, no, you’re not.” He tries to grab the phone out of Charlie’s hands, but she holds it out of his reach. He makes for it again when Sam smacks him on the shoulder.

“Come on, dude,” he says, “what’ve you got to lose?”

Dean stares at him, still in disbelief that they’re even having this conversation right now. “Uh, lessee,” he finally says, ticking off the reasons on unsteady fingers. “Vacation time, sanity, m’ fucking _pride_ …”

Sam opens his mouth to retort, but Benny shakes his head. “Leave him be, brother.”

Dean throws his hands up in victory. “ _Thank_ you. Somebody here’s finally talking some sense.” He drapes an arm across Benny’s shoulders. “C’mere, you handsome son of a bitch,” he says, squeezing his friend’s shoulder and planting a drunken kiss on his head. “Knew I could count on you, man.” 

Benny pats Dean on the shoulder while glancing over to Sam. “Ain’t your fault he’s too much of a chickenshit to do it.”

And if that whole remote shit from earlier had Dean feeling betrayed, it’s nothing compared to how he feels now as he immediately pulls himself out of Benny’s grip. “Uh, ‘scuse me?”

Benny chuckles, taking a sip of his beer as he regards Dean. “I’m just sayin’, brother. It’s about time you put yourself back out there, don’t you think?”

It suddenly feels like Dean’s gut’s bottomed out as he draws in a breath through his teeth. So _that’s_ what this is. “I’m not doing this right now.”

Charlie sets down the phone—still conveniently out of Dean’s reach, but at least she stops filling out the goddamn application. “It’s been two years since Lisa,” she says quietly. _Two years_ , Dean thinks. _Two years since he’d walked in on who he’d_ thought _was the love of his life fucking someone else on their kitchen counter. Two years since she’d picked someone else over Dean_. “Putting yourself out there might do you some good.”

“There’s a difference between putting yourself out there at a goddamn…” Dean waves his hand, frustrated as he tries to think up the right words, “...speed-dating night down at Dive Bar and putting yourself out there on national _fucking_ television.”

“True, but the point is, you’re not doing either,” Sam says.

Dean huffs. They’re right, he knows they’re right, but _admitting_ they’re right would mean that he’d have to make some changes, take some action, and he’s not ready for either of those things.

“No way I’m getting picked,” he finally mutters. When it came right down to it, he hadn’t been picked in his own _relationship_ , for fuck’s sake; what made them think a fucking reality show would be any different?

“Probably not,” Benny agrees, “but it’d be a hell of a time, wouldn’t it?”

Dean’s eyes dart up to Benny’s before moving over to Sam’s, then Charlie’s. None of them speak for a few seconds, until Charlie sets the phone down on the coffee table.

“Free dance lessons,” she says, elbowing him in the side with a smile. “In case you forgot, I’m expecting you to absolutely kill it on the dance floor at the wedding.”

Dean rolls his eyes and tries to look annoyed, but he can’t help but grin at the idea of Charlie and her fiancee, Gilda, fucking tearing it up at their wedding like he knows they will. It’s that, the idea of letting one of his best friends and her wife down on the biggest day of their lives (and only that, not the loneliness that he’s tried to stave off for so long now) that has him run a hand through his hair with a frustrated sigh of concession. 

“Gimme that,” he grumbles, holding his hand out for the phone.

* * *

Dean remembers the three of them referring to him as the Dancing King for the next few weeks—hell, Charlie even changes his name in her phone to reflect it—but that’s it. He doesn’t remember filling out the application form, doesn’t remember uploading a photo of himself, doesn’t remember hitting SEND, but apparently he fucking did each and every one of those things, because two weeks later he’d gotten a call from an unknown number congratulating him on being chosen as a contestant, and two weeks after _that_ , he’s standing at Buckingham Fountain, ruining the days of thousands of Chicago tourists who’ve come to see a fountain that’s now taped off for “a special event.”

 _Sorry,_ he wants to say. _Sorry I’m a lovesick idiot ruining your vacations to go through with something that’s destined to fail, but hey, can't say I didn’t try, right? Either way, though...my bad._

Instead, he tries to ignore the way his palms are sweating, the way his head feels light but heavy at the same time, the way he’s about to voluntarily make a fool of himself on national TV.

He loves his friends, but sometimes, just sometimes, he really fucking hates them.

The music starts to play around him, a faint instrumental version of the song that’ll run until they’re both in position and ready to start. He can hear shoes click-clacking on the stone, getting louder and louder as they approach him, and swallows nervously. Maybe it’s not too late to bail. This railing isn’t too high; he could hop it and just hurl himself into the fountain until they’ve got no choice but to leave him alone to drown his sorrows. He could just—

Two hands come to rest gently on his hips. This is happening, then. He takes a long, deep breath before letting the guy turn him around.

And fuck, if this guy doesn’t practically knock him _right_ on his ass first glance. Dean’s eyes start at the bottom, taking in strong legs and thighs, a simple white button-down with sleeves rolled up to the elbows (Dean hadn’t told him that’s a weakness in his application, had he? This is just fucking...luck of the draw? Jesus Christ), a royal blue tie (backwards, whatever, dude’s probably nervous), until he finally gets to his face.

If Dean had thought the _thighs_ were bad, they’re nothing compared to this guy’s eyes. Blue, blue, blue, blue. 

They’re real fucking _blue_ , is what he’s trying to say.

And just like that, Dean’s perfectly tailored pants aren’t fitting as well as they did before.

For a few seconds, all Dean can really do is stare. The guy takes a couple steps back, lips curling into a hesitant smile as he reaches his hand out—a hand that, Dean can’t help but notice, is infuriatingly _not shaking_. He’s checking Dean out too; he’s just somehow able to be less goddamn obvious about it, and frankly, that pisses him off too.

This is all riding on him; the music won’t start until he gets his ass in gear. He shakes his hands out, bounces on his toes for a few seconds, and, grinning in spite of himself, extends his arm and takes a step forward.

* * *

“You want me to _what_ , now?”

The choreographer, Anna, looks down at him from her position atop the edge of a prop bench, designed to look like the backless slabs of concrete Dean and his partner will be using in just a few days. She’s trying to be patient with him, which makes her a saint in Dean’s book, but it’s hard. He knows it’s hard. 

What’s _also_ hard, though, is trying to clear a bench with a side jump like he’s on the fucking high jump team.

“It’s not as scary as it sounds,” she says, redoing her ponytail before hopping off the bench and taking his hands in hers. She leads him over to one side of the bench and leaps back onto it like some kind of goddamn gazelle. “I’ll have you the whole time. All you have to do is jump—both feet together—and I’ll do the rest.”

He doesn’t say anything, but must still look like a nervous wreck, because Anna drops his hands and sits down on the bench, patting the spot next to her for him to do the same.

“Nobody here is a professional dancer, Dean,” she says, giving him a warm smile. “I’ll tell you right now, your partner definitely isn’t.”

Dean quirks an eyebrow at that. “We’re both shitty at this? Match made in heaven, then.”

She laughs, but Dean knows a pity laugh when he hears one—unfortunately—and clears his throat. “I’m probably drivin’ you up a wall, huh?”

“Trust me, it’s not you. All part of the job,” she says, shaking her head. “Anyone can learn some steps at least halfway-decently, enough for a quick TV spot, for sure. But a lot of what goes into a dance is trust. Not just in yourself, but your partner.”

“Well, if I knew that, I never would’ve signed up,” Dean jokes weakly. 

Another pity smile. “The worst that can happen,” she says, standing up and resting her hands on his shoulders so she can look him in the eye, “is that one of us will mess up, and we’ll try again. That’s it.”

While he appreciates that she didn’t just come out and say that _he’d_ be the one to fuck up, he can’t help but glance nervously at the camera crew in the corner of the room, still recording his every move. Anna follows his gaze and cranes her neck over his shoulder. With a single slashing motion across her throat—cut the cameras—she’s in charge, and Dean feels a hell of a lot better about the whole thing.

“Let’s take it from ‘grab me by the collar’ and see how it goes.” She grabs his hands once more and pulls him to his feet. He shakes his hands out, bounces on the balls of his feet as the PA cues up the music.

 _...You ain’t tryin’ to be wastin’ time on stupid people in cheap lines, I’m sure, I’m sure_ _  
_ _So I’d give a million dollars just for you to grab me by the collar..._

Dean takes a deep breath when Anna’s hand ghosts around the collar of his T-shirt as she struts around him, hopping up onto the bench in one fluid motion and holding out her hands. Dean takes them—he can do this, he can _do_ this—

_And I’ll come build us, build us…_

His feet leave the ground, but they’re not high enough. He trips himself up on the bench and stumbles hard, nearly smacking his face onto the bench and dragging Anna down with him in the process. 

“ _Fuck_ ,” he mutters, rubbing at his knee as he looks up at Anna. “Fuck, are you okay?”

She smiles at him, more amused than anything, and nods. “I’m fine. And you’ll be fine. It’s all part of the process, that’s what I want you to remember.” He opens his mouth to respond, but before he can, she continues, “What I _don’t_ want, though, is for you to write yourself off for this.”

“Oh, you mean for the fact that I can’t even jump over the short side of a goddamn bench?” It’s a little dramatic, sure, but Dean’s next action is to just drop to the floor, rolling onto his back to stare defeatedly up at the studio ceiling.

“Son of a bitch,” he mutters. Still lying on the floor, he holds his hand up and twirls a single finger in a pretty perfect mimicry of what he’s learned is Bella’s go-to mannerism, if he says so himself. “From the top, sweeties.”

* * *

Dean’s more surprised than anyone to see that it’s working, this thing’s actually fucking _working_. He knows the steps, and even though he can’t _not_ look at this guy, he’s sure-footed and confident and everything he’d never expect of himself when it came to dancing.

The song is pure sugar, straight out of a high school prom, with lines like _what a man gotta say, what a man gotta pray, to be your last “good night” and your first “good day”_ —cheesy—and _what a man gotta do to be totally locked up by you_ —kinky—something Dean normally wouldn’t be able to switch off fast enough.

But it’s making the guy smile, and that’s making Dean smile, and everything is just _good_. 

Everything’s second-nature. He can hear Anna in his head—“One, two, three; one, two, three; one, two, three... _good_ , Dean!”—and he remembers it all, the flows and step-ball-changes and body rolls that should feel awkward but just _don’t_ when he’s doing them across from this guy. 

They slide out and away from each other, arms extended, until Dean reaches for his hand, twirling him around and then extending his arm back out, being careful not to let go of his hand. The guy takes over at that, leading him over to the bench—and what Dean’s been dreading for days on end.

He keeps his back to the bench, trying hard not to shiver when he feels the guy’s hand ghost over his collar, from one shoulder to the other, before gently spinning him around and hopping effortlessly up onto the bench. Dean licks his lips, breathing in deep before taking the guy’s hands and looking up at him. When he does, the guy squeezes his hands—just a little, just enough—in reassurance, and Dean takes another breath.

He jumps.

He can feel the muscles in the guy’s arms go taut as he uses his upper body strength to lift Dean up and over the bench, landing him safely on the other side. It takes a millisecond (since that’s all Dean has, after all), for the idea that he made it to register—that he cleared that fucker with this guy’s help, by trusting him. Before transitioning into the next step Dean shoots him finger guns, a smile on his face that’s probably too wide and goofy for the occasion. Sue him, he just _cleared that goddamn fucking bench_ , and he’ll do whatever the hell he wants. 

The guy starts for a second, thrown off by Dean’s pose, but recovers quickly when Dean pivots back into the next set of steps. The guy takes his place in front of him and they roll their shoulders in opposite directions, turning their heads to maintain eye contact as they do so.

And if Dean takes an extra second or two to check out the guy’s ass in between shoulder rolls, that’s no one’s business but his own.

Before he knows it, the song’s wrapping up, and instead of the relief he’d been planning to feel, his brain is repeating _No no no no_. He doesn’t want this to end...or, okay, he _wants_ it to end, but it ending means that his dance, his date, his whatever-the-fuck with this guy is done. 

_What a man gotta prove? What a man gotta prove?_

Dean swallows hard as they grip each other’s forearms, spinning for two counts before breaking the contact to lean back, arms wide, hands splayed. 

_To be totally locked up by you? Totally locked up by you?_

Two more counts, and then they lean back in, pretending to unlock something (yeah, yeah, Dean knows it’s meant to signify their hearts, but he doesn’t need to admit that right now) with nonexistent keys. They throw the keys over their shoulders just as the song ends, left to stand just a few inches from each other.

Breathing hard, Dean grins at the guy in front of him, who looks just as pleased. They can’t say anything to each other—fuck, it was in their contracts that they couldn’t say anything, why the hell did Dean fucking _sign_ that—but before they go their separate ways, the guy reaches out and presses his hand gently against Dean’s cheek, and Dean goes still, leaning unconsciously into the touch.

The guy smiles, wide and gummy and genuine, and traces his thumb along Dean’s cheekbone for a second before turning around and walking away.

* * *

Dean thought the dancing was hard, but he’d forgotten about the waiting that comes afterward.

The dancing’s tough, sure, but the waiting? That shit’s excruciating.

It’s all part of the show: that blue-eyed adonis dances with two contestants (Dean being one of them), then, based on how the dances go, chooses which one he wants to see again. Dean knew this, he _knows_ this, but he hadn’t expected to end up so...smitten. 

Which leaves Dean, sitting alone at a too-small table in a too-cramped, too-hipster cafe, waiting too long to find out if that guy’s cheek pat was the real deal or just for show.

He’s painfully aware of the cameras around him as he sips his coffee, but this time, Anna’s not here to kick them out. He doesn’t even have his phone (prohibited on set, even for something as short as this), and he clears his throat uncomfortably.

“Hey, uh…” he ventures cautiously. “How long should I be waiting? I mean, it’s been a while, ri—ugh, fine,” he says, cutting himself off when the PA shakes her head.

He leans back in his chair, arms crossed over his chest as he stares up at the ceiling. They probably pitted him against some glamorous, cocky as hell dude without two left feet just to see him suffer. This is stupid. He’s wasting his time. He should just get up and go before he makes more of a fool of himself...what’re they gonna do if he tries to leave—tie him to the chair and force him to stay, record his misery for millions? 

Fuck that.

Decision made, Dean lets the front two legs of his chair drop to the floor. He scoops up his coffee cup and downs the rest of it in two gulps. He looks up to tell the PA exactly that—

And there he is. Looking flustered and a little panicked, the dude’s rushing toward his table (yes, he’s sure it’s his; he even glances behind him to make sure). Dean must be seeing things, though, because the second the two of them lock eyes, the guy’s anxiety just seems to...go away.

“I’m so sorry,” he says breathlessly, looking like he wants to grab Dean and plant one on him right then and there. “Our car got a flat tire and then we had to reshoot something, which makes _no_ sense, considering it wasn’t at all time-sensitive and they knew you were waiting here and...I’m sorry.”

Dean just stares at him for a few seconds, unable to do anything but grin. He picked him. This guy picked _him_. 

“Glad I stayed,” he finally says, then gestures for the guy to sit down across from him. “Figured you might’ve overslept after busting all those moves earlier.” He pauses. Does he joke? Does this guy like jokes? Well, Dean likes jokes, so fuck it. “Anna told me you suck at dancing, by the way.”

The guy pauses, then pulls out his chair and takes a seat at the table. “Funny,” he says, flipping open the tiny menu and glancing at Dean from above it, “she said the same thing about you...”

Dean chuckles, letting the silence hang heavy in the air for a few seconds before realizing that it’s his job to fill it. “Oh, uh, right. Dean.” He grins and extends his hand across the table for a shake. The second the guy’s fingers connect with his, Dean has to stop himself from sighing at the way he feels warm and sparking and _right_.

“Hello, Dean,” he says, eyes bright and kind and _home_. “I’m Castiel.”

**Author's Note:**

> Is this something you guys would want to see more of? I meant for it to be a sweet little one-shot, but I mean...they've eventually got to show off their skills at Charlie and Gilda's wedding, right?
> 
> For real, though, thank you for reading, hope you enjoyed, and are staying safe through all this <3.


End file.
